


The First Loves of Dean Winchester

by rw_eaden



Series: Canon 'Verse Snapshots [1]
Category: Supernatural
Genre: Biphobia, Bisexual Dean Winchester, Blow Jobs, Boys Kissing, Canon Compliant, Cunnilingus, F/M, First Time, Frottage, Internalized Biphobia, Kinda?, Kissing, M/M, Oral Sex, Vaginal Sex
Language: English
Status: Completed
Published: 2017-08-08
Updated: 2017-08-08
Packaged: 2018-12-12 17:16:39
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 1,866
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11741613
Author URL: https://archiveofourown.org/users/rw_eaden/pseuds/rw_eaden
Summary: The first kisses and first times of Dean Winchester.





	The First Loves of Dean Winchester

**Author's Note:**

> So, this is me, trying to beat back my depression with a stick. I've been a bit of a mess this past month so I figured, hey, why not write Dean being bisexual and stuff?   
> *insert shrug emoji*

Dean is sixteen the first time he kisses a girl. His heart is pounding so loud he can it like a drum beat in his ears. She leans over first, planting her soft lips against his, and it takes him a moment to get with the program. His lips are slow to move, too caught up in the shock of it all to really make an impression. It’s over all too soon, and he’s left dizzy, wide-eyed and stunned as she smiles down at her hands. Her name is Robin, and she probably won’t remember him in the years that come after this, but Dean’s never going to forget her.

* * *

 

Dean is seventeen the first time he kisses a boy. He’s got the hang of this thing now – the whole kissing thing – that is. He’s apparently good at it, and it’s a fun time for all involved. He’s in some small town in West Texas at the time, with a guy who he met at the county fair. He’d been wandering through the animal stalls, making faces at the sheep when he spotted that slick little smile underneath the brim of a cream-colored cowboy hat. His name is Aiden, and he’s much taller than Dean. He’s slim, all lean muscle and easy smiles and Dean thinks _fuck it_ – no one is gonna care. No one is gonna see him. He’ll be gone in a week or two anyway. They kiss after the sun sets, behind the Ferris Wheel, hidden in the shadow of the tall fence along the perimeter. Dean’s whole body shudders when Aiden licks his lips when his palms slide across Dean’s neck and his fingers edge into the ends of Dean’s hair. He smells like sweat and leather oil, and his groans cause Dean’s hips to jerk forward eagerly. He chuckles, easing Dean like a startled animal, drawing him forward with lips and teeth until they’re both breathless and giddy. They tease each other while throwing darts and gorging on fried cheese. Dean pretends his heart doesn’t hurt when his dad wrangles him and Sam into the car the next morning.

* * *

 

Dean is eighteen the first time he has sex with a woman. It’s not that he hasn’t had the opportunity, it’s just… well…what if something were to happen? He always uses protection but there are no guarantees. With the kinds of work he does, he sure as hell knows that. It’s just – logically Dean knows these women will never call him. He could try to give them his number, but there is no guarantee. Still, the possibility that sometimes life happens and if he does wind up with a kid out there somewhere, he would want to at least be old enough that if he did decide to leave the life his father wouldn’t have any legal hold over him.

Still, he goes to a bar and tries his luck. He’d prefer anywhere else, really, because the whole thing makes him feel like a skeevy perv and the smell of stale smoke, spilled beer, and furniture polish bothers his nose. He gets plenty of interested looks, but he feels out of his league. It’s not like he’s never seen a naked woman before, or done a little exploring, but he’s never gone all the way. He’s not sure what these women would expect from him, but he knows he’s going to embarrass himself. After two hours, he almost gives up but then he spots her. She’s alone, sighing wistfully and running her finger along the rim of a highball glass. She’s a brunette, her frizzy hair falling all over her face. Perhaps it had been up earlier in the evening, but now it’s a little chaotic. She’s not thin or dolled up like some of the other women in the bar, but she’s wearing make-up and a nice blouse. Probably just got off work. She’s young though, can’t be more than twenty-five. He watches as she glances over to a cluster of other women, similarly dressed, chatting with a group of guys near the pool tables.

Dean saddles up into the barstool next to her and introduces himself. Her name is Loreen and she has a beautiful laugh. Her cheeks round even more when she smiles and Dean really does want to listen when she speaks. She’s clever, too, and rolls her eyes at his lame lines but seems to be interested enough because she’s still talking to him. Eventually, he asks her if she wants to leave and she bites her lip but ultimately agrees.

They go to her place. She nervous, shying away just a little when his hands shim across her exposed skin. She crosses her legs, even though she’s naked intent on keeping his attention on her lips and the sensations she draws from him with her slender fingers. But that won’t do. She’s gorgeous, and he picked her not because she seemed easiest, but because she probably didn’t have expectations. But… that thought alone makes his stomach twist. She doesn’t have expectations likely for the same reason she keeps squirming under his gaze. He wonders how many men have neglected her, neglected to tell her that she is beautiful, and there’s nothing wrong with her.

He resolves to make it better for her than it is for himself. He trails his lips across her skin, kisses and kneads her breasts, trails his fingertips up her thighs and coaxes her legs open. It feels like he spends hours taking her in; the scent of her skin, the tremble of her limbs, the soft pleasured gasps. He doesn’t pay attention to his own dick until he can taste her on the back of his tongue and she’s no longer bothered by her own nudity. He throws his head back and groans when he slips inside her. He moves slow, drawing out the feeling of her warmth around him. It’s maddening and it’s amazing, and he’s barely holding on by a thread when she wraps her legs around his waist and moans into his ear. He’s never felt so completely in-tune with another person in his life.

In the morning, he leaves after she makes him waffles. He still gives her his number and thanks her for a lovely night. She kisses him on the way out the door.

* * *

 

Dean is twenty-three the first time he has sex with a man. It’s taken forever to get him to this point, and he’s probably still pushing it a bit. He’s terrified. His whole body is a single frayed nerve. Sex ed across America is shitty at best. He’s sat through at least six classes on the subject, and they range from “have sex and die” or “use a condom, you idiot”. Though, how to actually use that condom? His dad at least explained that part, thank whoever.  But when it came to sex with a man? Well, where the hell was he supposed to figure that one out? It wasn’t like he was going to ask his dad because the man probably didn’t know and might lose his mind if Dean asked. He wasn’t going to as Pastor Jim, that’s for damn sure. No, gay sex, like ganking monsters, is something that needs to be learned in the field.

The danger though is something he’s not sure he wants. He’s pretty, that much he knows, and his thick lips and long eyelashes put him in a distinct category. He’s the one to suck dick, to get fucked, to smile sweetly and flaunt his soft skin. But it’s not him. He’s gotten smooth with women over the years, flashing smiles and buying drinks and learning how to be both smooth and non-threatening. With men, though, he chokes on his own tongue. He can never figure out the right words, can’t pretend he knows what he’s doing, can’t come off as anything other than a terrified boy, and no one seems the slightest bit interested. It’s just… the idea of being vulnerable, of surrendering to another person who could hurt him

He’s in a gay club that’s too loud and too glitzy for his own liking, and he feels like an imposter. Hell, maybe he is. He likes women enough. He doesn’t have to even try with men, really. He has other choices. Maybe he just doesn’t belong. He’s not gay, but he’s not straight either, he’s – what was that called again – bisexual? Bisexual. But maybe bisexual is just code for “man who’s too chicken shit to get fucked so he sticks to women because it’s easier”. Maybe it’s code of “man who can’t choose while everyone else has to”.

Dean almost doesn’t notice when a new guy slides into the seat next to him. He’s big, not really buff, but not chubby either. He’s got a beard and he’s in jeans and an honest to god normal t-shirt, not the sheer fabric and pleather that populates the dance floor. He smiles, introduces himself as David, and asks if Dean’s waiting for anyone.

They make small talk, but David seems nice. He hasn’t mentioned Dean’s eyes or Dean’s lips, or Dean’s physique at all and Dean finds himself relaxing. He makes up a story about traveling for work and David buys it. He’s soft spoken and doesn’t push Dean to dance. They laugh, they drink, and when David asks if he wants to leave Dean agrees but insists on a motel.

David doesn’t ask any questions, he just kisses Dean and guides him through the doorway with a gentle hand on his hip. Dean’s hands shake when they strip each other, but David doesn’t seem to mind. He lets Dean set the pace before settling them down on the bed. He’s warm and solid against Dean’s body, covering him completely but not smothering. Dean allows himself to clutch at the back of David’s neck as the grind together.

He gasps and nearly shoots up the bed when David takes his cock into his mouth. Dean’s had blow jobs before, but never from another man. It’s not unfamiliar, though the scratch of coarse beard hair against his thighs is new. Dean whimpers when a finger circles lower, and clamps his legs shut involuntarily. For a moment, he’s certain he’s screwed it up and that’s the end, but David soothes him and clucks his tongue. They kiss and Dean gets lost in the feeling of lips across his neck and chest. He’s surprised when David gathers them both in a single hand and thrusts his hips. The slick, velvet heat of the two of them is incredible, especially combined with David’s gentle encouragements breathed into his neck. He losses it with his fists balled against a solid, muscular back.

David explains how sex with men works. Dean’s too timid to try it though, so when they’re both ready for another round Dean tries what David before. It’s not awkward, though he does need a little instruction, he doesn’t make Dean feel stupid or inept. When they part at check-in, David pulls him into a bruising hug and wishes him well, and Dean blushes and stammers his way through a goodbye and a thank you.  

**Author's Note:**

> I'm on the tumblrs, over [yonder](http://rosemoonweaver.tumblr.com/).


End file.
